Crystal Growth & Design Celebrates the International Year of

Dec 23, 2014 - A solid state structural phase transition accompanied by the order–disorder of the [NMe4]+ cationic guest in the host of perovskite-l...
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Crystal Growth & Design Celebrates the International Year of Crystallography 2014 Published as part of the Crystal Growth & Design virtual special issue IYCr 2014 - Celebrating the International Year of Crystallography Jagadese J. Vittal*,† and Javier Ellena‡ †

Department of Chemistry, National University of Singapore, Singapore São Carlos Institute of Physics, University of São Paulo, São Carlos, Brazil

‡

T

This virtual special issue covers a wide range of research topics in crystal growth and crystal engineering. In the crystal growth and crystallization process, Ikni et al. described an interesting laser-induced nucleation of carbamazepine crystallization,3 while Dikundwar and Guru Row have successfully trapped a metastable intermediate phase during the crystallization of 4-fluorobenzoyl chloride.4 In their contribution, Braga and co-workers investigated the effect of additives on the crystallization of bentazon, a commercial herbicide.5 In the area of weak interactions, Cavallo et al. proposed nomenclature for noncovalent interactions involving electrophilic sites.6 Further Bartashevich et al. attempted to understand the halogen bonding interaction in the crystals of dihydrothiazolo(oxazino)quinolinium oligoiodides in terms of electron density measurements.7 The significance of the charge assisted hydrogen bonding interactions was exemplified by Lou et al.8 Porous structures can easily be designed using metal ions and organic spacer ligands but to a lesser extent with organic molecules utilizing weak interactions. Interestingly, Patil et al. investigated to make void space in resorcin[4]arene-based supramolecular frameworks with various spacer molecules.9 The storage and handling of nitroaromatics are a major safety issue in the explosives industry. Vishnoi and co-workers demonstrated that the propeller-shaped C3-symmetric 1,3,5tris(4′-aminophenyl)benzene to be an appropriate supramolecular host for polynitroaromatic compounds including TNT.10 Mechanochemical grinding has been receiving major attention in green chemistry. Interestingly, in their contribution, Aznan et al. used liquid assisted grinding to replace piperazinium cation by DABCOH+ cation in an organic salt.11 Crystal engineering is beginning to play a major part in the pharmaceutical industry. In this respect, Kumar and Nangia take advantage of zwitter ionic forms to increase the solubility of pharmaceutical active pharmaceutical ingredients.12 On the other hand, the structural insights into the role of chloride anion on the biopharmaceutical performance of fluoroquinolone hydrochloride cocrystals were evaluated by Martinez-Alejo et al.13 Nanoindentation studies included in this virtual special issue showed that the cocrystals of saccharin with piroxicam yielded reduced plasticity and significantly deteriorated tableting behavior as compared to the coformers.14 Yao et al. described an interesting ionic cocrystal of 6-mercaptopurine

he orderly arrangement of atoms and molecules called crystal structures furnishes crystalline properties to the solids. The experimental science of determining the arrangement of atoms in the crystalline solids is known as crystallography. This is an important tool that is often employed by physicists, biologists, chemists, materials scientists, and engineers to determine the three- dimensional solid state structures. The physical properties are often controlled by the packing of molecules and crystalline defects. The understanding of crystal structures is an important criterion for understanding crystallographic defects. It is also a primary method of determining the structures of macromolecules by biologists. The United Nations declared 2014 to be the International Year of Crystallography (IYCr2014) to commemorate the centennial of X-ray crystallography since the first X-ray diffraction experiment was performed on a crystal of copper sulfate pentahydrate. The International Union of Crystallography (IUCr) has been actively publicizing the fundamental role of X-ray crystallography among scientists and students worldwide among various objectives to celebrate IYCr2014 (http://www.iycr2014.org/about).1 Engineering of crystalline materials requires an understanding of intermolecular interactions in the context of crystal packing and the utilization of such understanding in the design of new solids with desired physical and chemical properties. It is obvious that crystallography remains a vital tool in crystal engineering.2 The fast growth of crystal engineering in recent times may be mainly attributed to better understanding of the weak intermolecular interactions derived from X-crystallography. Hence it is not surprising that researchers and scientists in this area have been actively involved in IYCr2014 activities worldwide, and Crystal Growth and Design is no exception. A Crystal Growth and Design virtual special issue (http:// pubs.acs.org/page/cgdefu/vi/12.html) has been dedicated to celebrate the 2014 International Year of Crystallography (IYCr2014), and this is a compilation of selected papers that appeared and accepted in Crystal Growth and Design in 2014 by invitations and contributions. Thus, this virtual special issue hopes to provide a glimpse of various research activities in the fast growing field of crystal engineering. In this collection, we have contributions from a number of leading researchers from Australia, Brazil, China, France, India, Italy, Japan, Korea, Malaysia, Mexico, Russia, Singapore, Spain, Taiwan (People Republic of China), UK, and USA with the editorial by Prof. Gautam R. Desiraju in the first issue.1 Expectedly, the major contributors are from India and China. © 2014 American Chemical Society

Received: December 19, 2014 Published: December 23, 2014 2

DOI: 10.1021/cg501847a Cryst. Growth Des. 2015, 15, 2−4

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Crystal Growth & Design

spacer ligands in a number of pillared-layer MOFs from their work and published by others.35 The virtual special issue also has contributions describing the properties of MOFs. For example, Mao et al. investigated the luminescent properties of two new MOFs using a tetradentate pyridyl ligand and cyanide anion,36 whereas gas sorption properties of two pillared-layer MOFs were probed by Chen et al.37 Mellitic acid is a naturally occurring mineral that exists as its Al(III) salt. Clegg and Holcroft investigated the solid state structures of this carboxylate with various transition metal ions from design perspective.38 Overall, this virtual special issue to celebrate IYCr2014 covers almost all aspects of crystal engineering, comprising 37 articles from 16 countries. We wish to record our hearty condolences for one of our guest editors Oleg V. Shishkin (SSI Institute for Single Crystals, National Academy of Science of Ukraine, Kharkiv, Ukraine) who passed away on July 17, 2014. It is very unfortunate that he is not with us to witness this virtual special issue. Finally we thank all the authors for their contributions to this virtual special issue of Crystal Growth & Design.

with a Zn(II) complex to increase the solubility. Both coordinated and lattice water in the product could be removed in a single-crystal to single-crystal manner.15 The contribution by Pfrunder et al. discusses the details of different supramolecular structures formed by cocrystals of quaternary ammonium cations, halide anions (Cl− and Br−), and 1,2-, 1,3-, or 1,4-diiodotetrafluorobenzene showing interesting topologies.16 A solid state structural phase transition accompanied by the order−disorder of the [NMe4]+ cationic guest in the host of perovskite-like bimetallic azido coordination polymers was investigated by Du et al.17 On the contrary, different types of polymorphs of ditoluate derivatives of naphthalene 2,3-diol and phase transitions between them were described in a paper by Tamboli et al.18 Ellena and co-workers have elaborated a similar phase transition studies on estradiol-17β valerate in their contribution.19 Tidey et al. have encountered an interesting disappearing polymorph while investigating the properties of different polymorphs of [MCl2([9]aneS2O)] (where M = Pd(II) or Pt(II) and [9]aneS2O = 1-oxa-4,7-dithiacyclononane) which are rare in inorganic compounds.20 Various dynamics and reactivities of solids have also been featured in this virtual special issue. They include pedal motion,21 structural distortion due to guest exchange,22 structural transformation accompanied by dehydration,23 and solid state isomerization of rcttcyclobutane derivative to rtct-derivative in the coordination polymers.24 Apart from coordination polymers, crystal engineering of metal complexes, polynuclear complexes, and polyoxometallates by supramolecular interactions are of current interest. Some of the contributions in this area include the magnetic properties of calixarene-based nanocages by Su et al.,25 organic−inorganic hybrid rare earth derivatives of polyoxo anions,26 and Cu(II) azide polynuclear compelxes.27 Kundu et al. accomplished synthesis of a number of heterometallic coordination polymers using metalloligands through a sequential crystallization process.28 Furthermore, Uvarova et al. successfully assembled coordination polymers from porphyrin-based organophosphonate diesters with a [Cu2(O2CCMe3)4] paddle-wheel as the node.29 Exo- and endodentate coordination modes of macrocyclic ligands have been elegantly utilized to make one- and two-dimensional coordination polymers of Cu(I), Ag(I), and Hg(II) metal ions.30 Hawes et al. reported a number of new coordination polymers of Cu(II) and Co(II) derived from rigid and semirigid pyrazole-carboxylate ligands along with the coligand (S,S)1,4,5,8-naphthalenetetracarboxylic diimide-N,N′-bis(2-propionate) and studied their magnetic properties.31 Aiyappa et al. discovered a novel way to synthesize large Febased MOF crystals from a gel via PdCl2-mediated formic acid/ DMF oxidation.32 During the solvothermal process, Rankine et al. isolated a thermodynamic product at 150 °C, while a kinetic product Co-MOF was isolated at 65 °C. The kinetic product has been converted to a thermodynamic product by seeding the solution with the thermodynamic product Zn-MOF at a lower temperature.33 The paper by D’Vries et al. has shown that lower dimensional coordination polymers can coexist under different solvothermal conditions before forming the threedimensional metal−organic framework (MOF).34 Lee et al. nicely correlated the size of the net formed by metalcarboxylate layer and the degree of interpenetration due to

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AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. Notes

The authors declare no competing financial interest.

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REFERENCES

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Crystal Growth & Design (18) Tamboli, M. I.; Krishnaswamy, S.; Gonnade, R. G.; Shashidhar, M. S. Cryst. Growth Des. 2014, 14, 4985−4996. (19) Ellena, J.; de Paula, K.; de Melo, C. C.; da Silva, C. C. P.; Bezerra, B. P.; Venânci T.; Ayala A. P. Cryst. Growth Des. 2014, 14, 5700−5709. (20) Tidey, J. P.; O’Connor, A. E.; Markevich, A.; Bichoutskaia, E. N.; Cavan, J. J. P.; Lawrance, G. A.; Wong, H. L. S.; McMaster, J.; Schroder, M.; Blake, A. J. Cryst. Growth Des. 2015, 15, DOI: 10.1021/ cg500967w. (21) Harada, J.; Ogawa, K. Cryst. Growth Des. 2014, 14, 5182−5188. (22) Mukherjee, G.; Biradha, K. Cryst. Growth Des. 2014, 14, 3696− 3699. (23) White, K. F.; Abrahams, B. F.; Maynard-Casely, H.; Robson, R. Cryst. Growth Des. 2014, 14, 4602−4609. (24) Chanthapally, A.; Quah, H. S.; Vittal, J. J. Cryst. Growth Des. 2014, 14, 2605−2613. (25) Su, K.; Jiang, F.; Qian, J.; Gai, Y.; Wu, M.; Bawaked, S. M.; Mokhtar, M.; AL-Thabaiti, S. A.; Hong, M. Cryst. Growth Des. 2014, 14, 3116−3123. (26) Liu, D.; Lu, Y.; Tan, H.-Q.; Wang, T.-T.; Wang, E.-B. Cryst. Growth Des. 2015, 15, DOI: 10.1021/cg500955d. (27) Mukherjee, S.; Mukherjee, P. S. Cryst. Growth Des. 2014, 14, 4177−4186. (28) Kundu, T.; Jana, A. K.; Natarajan, S. Cryst. Growth Des. 2014, 14, 4531−4544. (29) Uvarova, M. A.; Sinelshchikova, A. A.; Golubnichaya, M. A.; Nefedov, S. E.; Enakieva, Y. Y.; Gorbunova, Y. G.; Tsivadze, A. Y.; Stern, C.; Bessmertnykh-Lemeune, A.; Guilard, R. Cryst. Growth Des. 2014, 14, 5976−5984. (30) Kim, H. J.; Park, I.-H.; Lee, J.-E.; Park, K.-M.; Lee, S. S. Cryst. Growth Des. 2014, 14, 6269−6281. (31) Hawes, C. S.; Moubaraki, B.; Murray, K. S.; Kruger, P. E.; Turner, D. R.; Batten, S. R. Cryst. Growth Des. 2014, 14, 5749−5760. (32) Aiyappa, H. B.; Saha, S.; Garai, B.; Thote, J.; Kurungot, S.; Banerjee, R. Cryst. Growth Des. 2014, 14, 3434−3437. (33) Rankine, D.; Keene, T. D.; Doonan, C. J.; Sumby, C. J. Cryst. Growth Des. 2014, 14, 5710−5718. (34) D’Vries, R. F.; de la Peña-O’Shea, V. A.; Hernández, A. B.; Snejko, N.; Gutiérrez-Puebla, E.; Monge, M. A. Cryst. Growth Des. 2014, 14, 5227−5233. (35) Lee, C.-H Wu, J.-Y.; Lee, G.-H.; Peng, S.-M.; Jiang, J. C.; Lu, K.L. Cryst. Growth Des. 2014, 14, 5608−5616. (36) Mao, L.-L.; Liu, W.; Li, Q.-W.; Jia, J.-H.; Tong, M.-L. Cryst. Growth Des. 2014, 14, 4674−4680. (37) Chen, Q.; Jia, Y.-Y.; Chang, Z.; Wang, T.-T.; Zhou, B.-Y.; Feng, R.; Bu, X.-H. Cryst. Growth Des. 2014, 14, 5189−5195. (38) Clegg, W.; Holcroft, J. M. Cryst. Growth Des. 2014, 14, 6282− 6293.

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DOI: 10.1021/cg501847a Cryst. Growth Des. 2015, 15, 2−4